I want the tic timer to fire every 60 seconds and show the 60 second count down in the status bar, but I want a 2nd countdown that counts down from 5 to 0 over 5 mins time and maybe even at the end of that time outputs "Beseech, Scribe, or brew time" or some such

The problem might be that the trigger capturing the prompt information needs to be marked Trigger On Prompt, and turn off Trigger On Newline. If Trigger On Prompt is not turned on, the trigger will not fire immediately--it will wait until a newline comes.